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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:43 UTC
HMDB IDHMDB0014715
Secondary Accession Numbers
  • HMDB14715
Metabolite Identification
Common NameSulfamethizole
DescriptionSulfamethizole, also known as rufol or thiosulfil, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. Sulfamethizole is a drug which is used for the treatment of urinary tract infection. Based on a literature review a significant number of articles have been published on Sulfamethizole.
Structure
Data?1582753212
Synonyms
ValueSource
RufolChEBI
SulfamethizolChEBI
SulfamethizolumChEBI
SulfamethylthiadiazoleChEBI
SulfametizolChEBI
SulphamethazoleChEBI
SulphamethiozoleChEBI
ThiosulfilKegg
SulphamethizolGenerator
SulphamethizolumGenerator
SulphamethylthiadiazoleGenerator
SulphametizolGenerator
SulfamethazoleGenerator
SulfamethiozoleGenerator
ThiosulphilGenerator
SulphamethizoleGenerator
Urgo brand OF sulfamethizoleHMDB
FNA brand OF sulfamethizoleHMDB
FNA, sulfamethizolHMDB
Sulfamethizol fnaHMDB
Wyeth brand OF sulfamethizoleHMDB
Chemical FormulaC9H10N4O2S2
Average Molecular Weight270.331
Monoisotopic Molecular Weight270.024516964
IUPAC Name4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
Traditional Namesulfamethizole
CAS Registry Number144-82-1
SMILES
CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1
InChI Identifier
InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)
InChI KeyVACCAVUAMIDAGB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Organosulfonic acid amide
  • Azole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Thiadiazole
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.61 g/LNot Available
LogP0.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.61 g/LALOGPS
logP0.53ALOGPS
logP0.21ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.71ChemAxon
pKa (Strongest Basic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.84 m³·mol⁻¹ChemAxon
Polarizability26.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.45331661259
DarkChem[M-H]-161.39931661259
DeepCCS[M+H]+157.08330932474
DeepCCS[M-H]-154.72530932474
DeepCCS[M-2H]-188.15230932474
DeepCCS[M+Na]+163.27930932474
AllCCS[M+H]+159.032859911
AllCCS[M+H-H2O]+155.432859911
AllCCS[M+NH4]+162.432859911
AllCCS[M+Na]+163.432859911
AllCCS[M-H]-155.332859911
AllCCS[M+Na-2H]-155.432859911
AllCCS[M+HCOO]-155.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfamethizoleCC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S14183.1Standard polar33892256
SulfamethizoleCC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S12600.9Standard non polar33892256
SulfamethizoleCC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S12998.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfamethizole,1TMS,isomer #1CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S12992.8Semi standard non polar33892256
Sulfamethizole,1TMS,isomer #1CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S12612.8Standard non polar33892256
Sulfamethizole,1TMS,isomer #1CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S14152.9Standard polar33892256
Sulfamethizole,1TMS,isomer #2CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S12675.9Semi standard non polar33892256
Sulfamethizole,1TMS,isomer #2CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S12510.1Standard non polar33892256
Sulfamethizole,1TMS,isomer #2CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S14033.0Standard polar33892256
Sulfamethizole,2TMS,isomer #1CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S12700.4Semi standard non polar33892256
Sulfamethizole,2TMS,isomer #1CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S12652.4Standard non polar33892256
Sulfamethizole,2TMS,isomer #1CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)S13491.9Standard polar33892256
Sulfamethizole,2TMS,isomer #2CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S12818.4Semi standard non polar33892256
Sulfamethizole,2TMS,isomer #2CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S12734.0Standard non polar33892256
Sulfamethizole,2TMS,isomer #2CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S13891.5Standard polar33892256
Sulfamethizole,3TMS,isomer #1CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S12625.0Semi standard non polar33892256
Sulfamethizole,3TMS,isomer #1CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S12765.2Standard non polar33892256
Sulfamethizole,3TMS,isomer #1CC1=NN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)S13288.3Standard polar33892256
Sulfamethizole,1TBDMS,isomer #1CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S13250.8Semi standard non polar33892256
Sulfamethizole,1TBDMS,isomer #1CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S12839.7Standard non polar33892256
Sulfamethizole,1TBDMS,isomer #1CC1=NN=C(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S14146.6Standard polar33892256
Sulfamethizole,1TBDMS,isomer #2CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S12929.9Semi standard non polar33892256
Sulfamethizole,1TBDMS,isomer #2CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S12741.4Standard non polar33892256
Sulfamethizole,1TBDMS,isomer #2CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)S13995.2Standard polar33892256
Sulfamethizole,2TBDMS,isomer #1CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S13205.6Semi standard non polar33892256
Sulfamethizole,2TBDMS,isomer #1CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S13110.2Standard non polar33892256
Sulfamethizole,2TBDMS,isomer #1CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)S13529.9Standard polar33892256
Sulfamethizole,2TBDMS,isomer #2CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S13366.1Semi standard non polar33892256
Sulfamethizole,2TBDMS,isomer #2CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S13178.1Standard non polar33892256
Sulfamethizole,2TBDMS,isomer #2CC1=NN=C(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S13880.3Standard polar33892256
Sulfamethizole,3TBDMS,isomer #1CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S13348.5Semi standard non polar33892256
Sulfamethizole,3TBDMS,isomer #1CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S13441.6Standard non polar33892256
Sulfamethizole,3TBDMS,isomer #1CC1=NN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)S13416.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamethizole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9520000000-612be3b68261ab7e44e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamethizole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamethizole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethizole LC-ESI-qTof , Positive-QTOFsplash10-0a4i-6921000000-126773aad654d2eed32d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethizole LC-ESI-QTOF , positive-QTOFsplash10-0a4i-1900000000-d28aaee868ff14cf276c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethizole , positive-QTOFsplash10-0a4i-2930000000-baa3fcc8543e75aae1502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethizole , positive-QTOFsplash10-0a4i-6921000000-126773aad654d2eed32d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethizole -1V, Positive-QTOFsplash10-0a4i-1900000000-be6bc1fbe226f471ada12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 10V, Positive-QTOFsplash10-0fk9-0190000000-65b647815b272c2113432016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 20V, Positive-QTOFsplash10-0pi0-1980000000-7fadab7f248de98fdf2f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 40V, Positive-QTOFsplash10-0v0r-9020000000-38dd107f4616bd2bbcf52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 10V, Negative-QTOFsplash10-014i-0090000000-e6595fd414c0072675742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 20V, Negative-QTOFsplash10-02t9-1490000000-e623f31f5c64f3fc4b1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 40V, Negative-QTOFsplash10-0a4i-5920000000-b4846ad87d713bf15d8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 10V, Positive-QTOFsplash10-0ab9-0940000000-5f9fea338a3259e1358b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 20V, Positive-QTOFsplash10-0a4i-4900000000-294de38d9541211580c52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 40V, Positive-QTOFsplash10-014i-9000000000-c0447fdeace53d9b33ef2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 10V, Negative-QTOFsplash10-014i-0090000000-37863beaac79d46e4d4d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 20V, Negative-QTOFsplash10-066r-1690000000-571175f48422a730717e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamethizole 40V, Negative-QTOFsplash10-0a4i-2900000000-98411d72ae7ea399e4302021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00576 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00576 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00576
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5137
KEGG Compound IDC08050
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfamethizole
METLIN IDNot Available
PubChem Compound5328
PDB IDNot Available
ChEBI ID9331
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. [PubMed:2372557 ]
  2. Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. [PubMed:12604534 ]
  3. Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. [PubMed:14519675 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]